Dimethylformamide dimethyl acetal → 5-nitro-1H-isochromen-1-one

Participants

Reaction Steps

16.4 g (84.03 mmol) of 2-methyl-3-nitrobenzoic acid methyl ester is stirred with 26.8 g (225.1 mmol) of N,N-dimethylformamide dimethylacetal in 85 ml of dimethylformamide for 12 hours at 130° C. The solvent is drawn off in a rotary evaporator, the residue is taken up in methyl tert-butyl ether and washed three times with water. After washing with saturated NaCl solution, the organic phase is dried. After the dessicant is filtered off and after the solvent is spun off, the remaining residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 8.73 g (54.4%) of the desired compound is isolated.

Provenance & Evidence